


The first time doesn’t ALWAYS go as planned.

by Sorceress_Supreme



Series: Two dorks in love [2]
Category: Batman (Comics), Batman - All Media Types, Batman Eternal, Red Robin - Fandom
Genre: Dating!, Harper and Jay give a variation of the sex talk!, M/M, Mentions of Sex, Tim and Cullen go on a date!
Language: English
Status: Completed
Published: 2014-09-25
Updated: 2014-09-25
Packaged: 2018-02-16 22:54:20
Rating: Teen And Up Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 3,846
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/2287475
Author URL: https://archiveofourown.org/users/Sorceress_Supreme/pseuds/Sorceress_Supreme
Summary: <blockquote class="userstuff">
              <p>Tim and Cullen go on a date and both worry about if they're going to have sex.</p>
            </blockquote>





	The first time doesn’t ALWAYS go as planned.

**Author's Note:**

> Ok so I thought I should write about one of Tim and Cullen's first dates and well...their first time having sex with each other. Or at least their first discussions on the matter. Maybe I'll write their first time? Who knows?

The first time doesn’t ALWAYS go as planned.

  It’s been a month since Cullen had started dating Tim. The dates were nice and varied from walks in Robinson Park to eating at Tim's penthouse or his place in Crime Alley. And it was all wonderful! Cullen was going out with his crush! He hadn’t felt this happy in a long time. Though there was one thought that kept nagging him in the back of his mind. “ _What about sex? You’re a virgin and He’s probably done it before!_ ” It would show up lately during their time together and he’d start getting flustered causing Tim to worry and place his hand on Cullen's face and god they were soft…despite still being covered in calluses.

  He hated making Tim worry so much about him. But he didn’t know how to tell him that he kept thinking about what would happen if and when they finally had sex. So? He stayed quiet. Though it seemed like his dreams had other plans for him. Most nights he’d dream of Tim kissing him and running his hands all over Cullen until he finally started to open him up and fuck him. Others it was slow and tender with soft kisses and even softer touches.

  For Tim? His dreams were all soft and romantic. He was tired of the rough handling he got from Patrols and fights and well…what’s wrong with wanting to be gentle once in a while? He wanted to do that with Cullen. To hold him close and whisper to him how much he loved him. Course that took planning. He had to get everything right! But how? On the one hand? He could just take him out to a fancy dinner just the two of them…course that might make him uncomfortable.

  As such he was struggling on how to go about this. He hated that yes he was now living up to that DAMN nickname “The Virgin Wonder.” Which? HE WASN’T! Oh my god guys! He’d had sex before! With Kon. And god it had been good. Course they’d also been under the influence of Sex Pollen from Kory’s new alien fern. Actually there might’ve been a tower wide orgy…The details are sketchy. But he WILL maintain he only went for the D. NOT any of the girls…ok he might’ve made out with rose. Then she might’ve gone and fucked Cassie in front of them...again details are now a bit fuzzy.

  But back to the crisis at hand. Cullen, sex and how to have such without making a fool of himself or making Cullen feel like he HAS to put out. Oh god…where’s the booze…oh…right…he’s not allowed to drink because he’s 19…DAMMIT! Still getting drunk wouldn’t help him at all so he started looking through his contacts to find Barbara’s number and prayed she wasn’t busy with work for her actual job or the Birds of Prey. Or uh…that he didn’t interrupted her having sex with dick and Kory…in any combination.

  After he found it he dialed and set his phone on hands free. “Goddess of Knowledge and Badass at your service speak your plea mortal.” Came Barbara’s reply making Tim smile. “Hey Babs. I need help. I’m trying to well…um…” he couldn’t find the words cause Babs was like his older sister and this was awkward! “Does it involve Cullen and sex? Cause I got a call from him earlier about that.” That brought Tim's mind to a screeching halt.

  “He did? Oh god…what did you tell him!?” Babs laughed and smiled watching the screen with her Drake-Cam of Tim's place. “I told him you’re just as new to sex with a man as he is. That you’re only time at gay sex involved sex pollen and titans’ tower. And? That you wouldn’t force him. Ever.” Sighing in relief Tim relaxed into his chair. “Ok…now…got any suggestions for a restaurant?”

  A few days later Cullen got a phone call from Tim. “Hello?” “Hey. I uh…I got us a reservation at a nice place Babs suggested…Oh right it’s Tim. Sorry…um…” Cullen smiled. “What’s the dress code? And um what kind of place is it?” Tim sighed softly with a grin. “It’s laidback. A bit pricey. But? The food’s supposed to be amazing. So sorry to spring this so suddenly…I didn’t think and-” He was cut off by Cullen's reply. “Ok. How long until you come get me?”

  “Does half an hour maybe 45 minutes sound ok?” Tim asked grabbing a cardigan from his closet. “Sounds perfect. See you then.” “Bye Cullen.” Tim said and they both hung up to freak out over what to wear and over if sex would happen…which? They both hoped would. Cullen smiled as he looked through his closet pulling out a nice shirt and a hoodie. “What’s got you so smiley?” Harper asked looking in. “Tim's coming to pick me up for a date!”

  Harper grinned and walked over. “That’s great. Need help picking out clothes again?” Cullen held up his choices. “I think? I don’t know? He said it was laidback so I um…ok help.” Harper kisses his head and helps him choose his clothes. “Ok so I think the red sweater will work. The one with the 75 on it?” She said holding it up. “Wasn’t that the one I was wearing when…I went into that coma?” he asked wincing a little. “Yeah. But? I think that means you can make it good.” Cullen nodded before taking it and pulling it on over his plain shirt.

  “Hey…Harper? If…Tim and I um…have sex…well…” He blushed almost as red as his sweater. Harper turned to him and set down the jacket she was holding and hugged him. “Then I hope you and him are safe. Cause god I just want you to be happy. Got it?” She said kissing his forehead. “I got it sis. So any tips?” he asked with a small grin. “Yeah. Lube is your friend. Use a ton of it. Also? Condoms. Unless you both agree not to use them. And IF you don’t want to have sex? Say no. A lot. I know Tim's not the kind of guy to push but I still want you to be clear on this.” Cullen nodded with a soft smile. “Right.”

  At the Theater? Tim was looking for his glasses. His contacts were missing and he was half blind in his search. “Found’em! Haha!” with a cry he put his glasses on. “Ok now for the earrings…’ he muttered looking on his dresser for some of his earrings to wear. “Hey Red Hipster.” Jason said from the doorway. “JEEZ!” Tim jumped a bit, “How’d you get in here?”

  “The door. You getting ready for your date?” He asked walking over to Tim and straightening his cardigan. “Bet it was a shock when he learned YOU were the tattooed and pierced punk and I was the goody two shoes.” Tim smirked and hugged him. “Yeah…so…should I put my earrings in?”

  Jason stepped back to survey his little brother’s outfit. “Hmm. I dunno you’re already walking a very fine line clothing wise between 90’s Grunge and Millennial Hipster.” He said and Tim groaned. “WHY do those two styles have to be SO similar?!” came Tim's reply as Jason walked over to the dresser and started looking for one of Tim's labrets. “You could just put the labret and those ear cuffs that look like a skeleton hand on one ear and the Robin symbol on the other.’ Jason says walking back to Tim with the jewelry. ‘But make you your mind quick. You said you’d be there in how long?” Another groan from Tim as Jason chuckled.

  “Half an hour. I still have 20 minutes before I’m screwed.” Tim said before looking and taking one of his labrets and putting it in. It was a simple black stud but it worked with the rest of his outfit. “Ok now that that’s settled. You plan on sex with Tweety Bird?” Jason said grabbing Tim's messenger bag and double checking the contents for things like his umbrella, spare shirt and his meds.

  “Yes. I already put the condoms and lube in my bag jay. I just…I dunno if he’ll want to.” Tim said sitting down on the foot of his bed. “Then you respect that.’ Jason held his hand up when it looked like Tim would protest, ‘I know you’d NEVER force anyone. But I’m just making sure ok? Older brother duties. Also? NO drunk sex if you DO somehow manage to get alcohol into either of you. I don’t care if you think you’re not THAT drunk. NO DRUNK PEOPLE SEX. You WILL get hurt doing something stupid.”

  Tim laughed with a smile. “Ok. No sex drunk and respect his choices. I got it. You gonna end up stalking us on our date?” he asked taking out his wallet to double check he had his money and all his important cards. “Nah. I’m gonna go do my own thing.” Tim raised an eyebrow as he got up and accepted his bag back. “Does it involve a certain monk?” Jason blushed and shoved Tim out of his bedroom and to the door snagging his keys along the way. “Shut up! There is NOTHING going on between Mr. Can’t understand WHAT a secret identity is and me!”

  Tim grinned and took his keys. “Uh huh. Jason? Thanks.” He said opening the door that lead to the stairs down to the main entry way of the Theater. “Yeah sure. Knock’em dead kid.”

  Once Tim got to Harper and Cullen’s apartment he knocked on the door and grinned when Harper opened the door. “Hey Harper. Is Cullen ready?” he asked as she let him in. “What no flowers? And yeah he should be down in a minute.” She replied. They heard a crash and a cry of “I’m Ok!” as Cullen rushed in. “Sorry. I um…hi.” He said with a weak smile as he looked at Tim. “It’s alright I just got here. Are you ready?” Tim asked as he went over to him. Cullen straightened up and grinned. “Yup!”

  Harper grinned at the couple. “Ok now get going so you can make your reservation and call me if you end up staying at his place ok?” “Yes Harp!” Cullen said as Tim chuckled. “Of course Harper. “ Harper nodded. “Good now get going! And be safe!” She called out as Cullen shut the door and started blushing. “ _Dammit Harper! Now he’ll think I’m gonna jump him!_ ” Cullen thought as he walked with Tim to the elevator.

  Cullen sighed as he got in, “ _Of course I wouldn’t but..._ ” His thoughts cut off when he felt a soft kiss being pressed to his lips as the doors shut and the elevator moved. “Hey…you sure you’re ok?” Tim asked softly his head tilted to the side slightly. “Yeah just...over thinking things I guess.” Came Cullen's reply as he leaned his head on Tim's shoulder. “I see. Should I ask about what? Or is it something private?” Cullen raised his head and looked up at him. “It’s just…kind of embarrassing.” He muttered with a slight blush.

  Tim hugged him as the elevator stopped at the ground floor and opened. “I see.” Tim said as he led Cullen out and into the foyer of the apartment complex a smile on his lips as Cullen held onto his hand. “It’s about well…’ He said as they headed for Tim's car in front of the building. Tim opened the passenger door to let Cullen in before going to the driver’s side. ‘Um…never mind.” Cullen sighed and buckled up. “Are you sure Cullen?” Tim asked as he buckled himself up and started the car.

  “Yeah. I’m sure.” He said as Tim drove. “Ok. So you ever read The Maze Runner? Steph says I look like Dylan O’Brien...Actually Jason might’ve told her that…” Tim said muttering the last part. Cullen laughed and smiled at him. “No haven’t read it but yeah you DO kind of look like him. And dress like Stiles or Sam Winchester.” Tim groaned “And that I have Cosnia’s glasses?” Cullen considered that. “Yeah but also a bit of Percy Jackson’s sass combined with Nico di Angelo’s dry snark and Thalia Grace’s taste in music.”

  Tim hummed thoughtfully as he stopped at a red light. “So I’m the love child of the Greek Kids of the Big Three? Nice.” Cullen smiled at him. “Yeah…though that’s just my opinion. Hey you know those um…Funko vinyl dolls? Harper found some at Hot Topic. They have um…Elsa and Belle and she said I should get you them.” Tim looked at him as he drove once the light turned green. “I have a couple of those actually. Nightwing, Superboy and myself as Robin. Still looking for Babs as Batgirl and waiting for them to make Bart as either Kid Flash or Impulse.”

  “What no Groot?” Cullen asked as Tim turned the car out of Crime Alley and into the nicer part of the East End that led to the Diamond District. “Oh THAT is a given. BOTH versions of Groot. The adult AND the dancing Baby Grootling! I want a dozen or more of the grootlings to program to dance so I can freak Bruce out when he comes into my office to talk.” Came the reply from a grinning Tim. Cullen smiled and relaxed into the seat of the car.

  As soon as they arrived at the restaurant and Tim parked Cullen bit his lip looking around nervously seeing all the nice and expensive cars. “It’s ok Cullen. I promise.” Tim said holding Cullen's hand in his own his thumb rubbing the skin between Cullen's knuckles. This got a contented sigh out of Cullen as Tim increased the pressure a bit before letting go and kissing Cullen's cheek.

  “Tim? Um…thanks.” Cullen said blushing softly. “For what?” Tim asked looking at him as he fidgeted with the hem of his shirt. “For liking me and…Well taking a chance on Harper and myself.” He felt his cheeks heat up as Tim's mouth twitched into a small smile. “I understand. You were well…I felt a bit responsible for you falling into that coma…and I didn’t…I didn’t want Harper going out looking for a cure without a clue. Course…she ended up HACKING me and well…’ he broke off chuckling as Cullen laughed, ‘Yeah she hacked me while you were in a coma and ended up stowing away on my plane. But over time? I came to know that she loved you as much as I love my own siblings. And as for you?”

  Cullen looked at him his eyes worried. “I came to love you dearly.” He leaned down a bit closing the couple of inches that separated them in height and kissed him. Cullen leaned into the kiss sighing softly as Tim wrapped his arms around him. After he pulled back to breathe Tim's lips quirked into a kind of half smile. “Feel better now?” Cullen nodded as they headed inside the restaurant. Once at their table Tim looked over the menu. “ _Ok this is going well. Nothing is going wrong! No batman crashing through the windows! No villains! Finally! I can have a normal date!_ ” He thought as he surveyed the options for food and drinks.

  As he considered his options he peeked over the tops of his glasses and his menu to look at Cullen. “ _He looks happy. Wonder if he’s found something he wants to eat? Course I’m still looking. And well if he wants to well…if he wants to do it. I hope he does. If not? Ok._ ” Soon the waiter came over to take their orders. “Should we share something? I mean if you want too…”  Cullen said blushing at Tim. He smiled as he replied “That’s a good idea. They have a pasta dish we could try. It’s a kind of fettuccini? “That got a shy half smile from Cullen in return, “Sounds great! Now what to drink?”

  “The lemonade looks good. We could have that.” Tim suggested and Cullen nodded in agreement. “Ok so we’ll have two lemonades and the fettuccini to split please?” Tim asked the waiter who nodded and wrote it down. “Will that be all for now?” “Yes. Thanks.” Cullen said still blushing as he and Tim handed their menus to the waiter who walked off to place the order.

  Tim smiled at Cullen and laid his hand over his. “You ok?” He asked squeezing the hand marveling at how soft it was compared to his own. “Yeah. You?  I mean this is…umm...it’s nice. I guess I’m just…guess I’m a little nervous.” Cullen replied and was once again blushing. Tim lifted the hand to his mouth and kissed it softly. “There’s nothing to be nervous about. I promise.” Cullen smiled and it was soft and sweet making Tim's heart flutter a bit.

  “I know but…well…I keep thinking and…” He trailed off and Tim watched him seeing how his shoulders hunched like he was trying to hide inside his sweater a move Tim himself has used many times be it Tim Wayne’s suit jacket or Red Robin’s cape. “ _I keep thinking this is going to lead to sex and I want it I do! But…I don’t know if I do…does that make sense?_ ” He thought to himself peeking at Tim from under his bangs. “Cullen? You can tell me. I promise I won’t laugh or do anything stupid in response to whatever it is that is bothering you.” Tim said rubbing at the skin of Cullen's knuckles like when they’d first met in Tim's office at WE.

   Before Cullen could respond the waiter returned with their drinks and informed them that it should be another ten minutes before their meal was ready and left. Cullen took a sip of his lemonade and his eyes widened. “Oh wow…this is really good! Tim? What do you think?” He asked looking at him as Tim took a drink from his own glass. “Mmm…perfect blend of sweet and tart. And…I think they put blackberries in it too. What do you think?” Tim asked and Cullen took another sip.

  “You’re right! It’s a bit faint but it’s there. I really like it.” Cullen said smiling at Tim. With a light chuckle Tim released Cullen's hand and picked up his drink again savoring the flavors. “So Tim? If we go to your place? Umm…’ Cullen paused to take a drink of his lemonade as Tim placed his hand on his again, ‘If we do you um…n..nevermind. I’m just babbling. It’s nothing forget it.”

  “Cullen. If something is worrying you? I’d like to know…if that’s ok?” Tim said gentle and earnest. Cullen bit his lip knowing he should tell Tim why he was worried but he didn’t want to ruin their date. “Later…I promise.” He said as the food came out and was set down in between them. Tim nodded and let go of his hand and Cullen hated the loss of it.

  Tim took a forkful of the pasta and held it out to Cullen. With a half smile Cullen opened his mouth to accept the fork of pasta moaning slightly at the taste. “Mm…it’s so good!” He said as Tim grinned and ate some having the same reaction that Cullen had. “So did you hear about the Selection Series news?” Cullen asked and Tim held up a hand. “No not yet. So no spoilers please.” And as fate would have it? Tim's cell phone went off with a text from Steph the tone of course being River Song going “Spoilers.”

  Cullen chuckled as Tim looked and texted her. “Sorry. She’s wondering how the date’s going and I told her that well, it’s going fine.” He said sheepishly.  “It’s ok. So? More pasta?” Cullen said offering his fork to Tim who smiled and ate the offered food licking his lips for excess sauce making Cullen blush a bit. He then twisted his ankle around Cullen's lightly.

  Later once they had finished dinner and paid they headed to Tim's place. The whole ride Cullen's stomach turned. “ _It’s just a movie and some dessert! Nothing more! Right? Yeah. Just a movie…and…dessert…_ ” Cullen's thoughts trailed off as he felt a hand on his thigh. “Cullen? You ok?” Tim asked and Cullen sighed. “I’m just over thinking things… Like is this JUST a movie and dessert or it code for something else…I know you’d never force...” He trailed off biting the inside of his cheek.

  Tim nodded softly. “I understand. I kind of planned on the possibility we might have sex. But? If that makes you uncomfortable? We’ll just watch a movie and eat dessert. I promise.” He looked over at him and nodded. “Ok. I can do that. So what’re we watching?” He asked relaxing into the seat of the car as Tim drove. “I was thinking we could watch ‘The Princess Diaries’ that ok?”

  “Yeah it’s ok. Hey you ever notice how Selina looks kind of like Anne Hathaway?” That got a laugh out of Tim. “Yeah and B looks like Christian Bale some days. Sounds like him too! I’ve all but convinced Helena that he’s Howl from the movie!” “So do you actually have any of the projectors running?” Cullen asks as they park in the garage cause hey? Boyfriend lives in an old movie theater? He’s GOT to have at least ONE of the projectors running!

  Grinning as he gets out and opens the door for Cullen “That I do. It’s just nice to be able to watch them on the big screen even if it’s a dvd.” He says as they head into the stairwell in the garage that leads to the upper floors where Tim lives. After they put their things on the couch Tim started to grab some plates and a half of triple layer chocolate cake.

  “I thought you couldn’t eat that?” Cullen said as he helped get some glasses for drinks. “What Alfred doesn’t know won’t kill me.” Tim replied as he sliced the cake so they’d have a small piece each. Placing them on the plates Tim looked at Cullen and hugged him once he set the container of juice down. “Tim? Why’re…” Tim kissed Cullen's temple softly. “Just thought you could use a hug is all.”

  Cullen turned in the hug so he could face Tim. “Thanks…really.” He said hugging him back tightly. Tim smiled and rubbed small circles on Cullen's back swaying slightly. “Maybe we should just stick to the couch then? Much comfier than movie seats.” Tim suggested as Cullen pulled away a bit to look at him. “Yeah that sounds perfect.”


End file.
